Wendy Lea talks about the risks of saying no

Entrepreneur, investor, and Techstars board member Wendy Lea remembers the beginnings of Techstars, her first encounters with #GiveFirst—and how mentors have changed her life.

Wendy Lea is a longtime entrepreneur and investor, as well as a board member and mentor at Techstars. With David and Brad, she digs into some of her first mentoring experiences and reflects on a time when a mentor changed her life.

Wendy was early in her career and had just been offered a promotion that would cause a lot of change in her life, and she was hesitating. Her mentor told her: the risk of saying no is very high. “If you say no, you’re playing small. You have a lot of potential, and you need to go explore that potential.”

She did, and she traces her success back to that encouragement and good advice.

Listen for more about the risks of saying no… and saying yes.

Bonus: Listen to Wendy, David, and Brad reminisce about the first Techstars class.

An edited transcript of the conversation follows:

David: We’re really excited to have Wendy Lea here as a guest today on the podcast. Wendy is a board member at Techstars, and she recently moved back here to Boulder after spending four years in Cincinnati as the CEO of Cintrifuse. Welcome, Wendy.

Wendy: Thanks a bunch. That was a fun gig by the way, Cintrifuse. I’ll end on that.

David: Spend a few minutes giving us your origin story.

Wendy: A little bit about my background might help those of you listening grok my experiences and where they come from. My big success came with a company called OnTarget, and it came after lots of professional training in large companies. With OnTarget, three or four of us worked like dogs to make that work around the world. We owned it 100%, and we sold it for $150 million to Siebel Systems in 1999.

After that, I worked for Siebel, which was fantastic. I loved that because I learned a lot, and then I took that experience and started doing new things with it, for example, really working with venture-backed startups. That was very different: the risk, the reward, and the kind of mentoring that startups required. It was this that brought me to Boulder. In Boulder, I worked with companies like Lead Works—formerly Duo—and also Numerics.

Then I went to California. I made a bunch of angel investments and I did a big tour of duty at Get Satisfaction. Get Satisfaction was a big love, my biggest love in all of my work life. It didn’t turn out as planned, but it was quite remarkable. I’m back here in Boulder now, and proud to serve on the Techstars advisory board.

Brad: Wendy, would you talk a little bit about how you got introduced to Techstars and what your involvement with Techstars has been?

Wendy: At the very beginning it was an ask from you to plug into the community. From there you introduced me to David, and David told me about his big idea about bringing entrepreneurs and mentors together. That’s the first time I heard about Techstars, and that was the first cohort. I’ve hung around with a lot of mentors, and I became plugged in through the community that Techstars created here in Boulder.

David: Back then, that was really the first super visible example of Give First in Boulder. There were so many mentors who were trying to help that first class of 10 companies—which turned out to be a great class—and get this whole mentorship-driven accelerator thing going.

Tell us about your biggest lesson as a mentor.

Wendy: My biggest lesson as a mentor was with a company called EventVue. The founders, Rob Johnson and Josh Frasier, had an idea that was completely easy to understand. It wasn’t complex and crazy. I really got it and I liked what they were doing.

They were very, very early in their life cycle as entrepreneurs and they were impressionable. If a mentor told them something would work out, they really believed it. It was a struggle because I didn’t want to dispute other advice they were getting, but I suspected that the situation wasn’t going to work out. That was tricky, because you want to be upbeat. I believed in what they were building, and they were working like dogs. Of course, it didn’t work out.

Now when I see them, they always say, “Oh, I’m so embarrassed when I look back and think that I was so cocky.” And I say, “You know, it happens.”

David: So you were trying to manage that dynamic.

Wendy: I was trying to manage their expectations. This was before all the cool modules that we have now in mentoring, it was just us bushwacking through, doing what we could to give back. It was tricky. I did what I was taught as a young woman: ask a lot of questions, and see if they’ll tune into that reality or not.

Brad: Wendy, you’ve been involved in lots and lots of companies, both as a founder or entrepreneur, and you’ve been brought in by a bunch of startups to help by serving on their boards. You’ve also been a startup investor. When you reflect on all of those experiences, what’s the most fun you’ve had with a company?

Wendy: Building out the leadership teams.

Brad: Can you talk us through an example?

Wendy: On the venture backed side, it was awesome building out the team at Get Satisfaction. It was also hard.

Brad: What were some of the awesome things?

Wendy: We were really trying to figure out the match between the skills and knowledge that were being represented, and the needs we had on the team. We hired someone, and it turned out we brought in the completely wrong person.

He didn’t know how to get his hands really dirty: sit with the engineers and talk with them directly about what they saw in the code. The code needed to be refactored. It was going to be an expensive proposition. We all kind of knew that, but the guy was saying all the right things. He affiliated more with the product managers, and not with the engineers, and it caused problems.

That was a significant turning point for me, because I don’t have that background. I had to listen and learn and ask the founders. It was exciting and scary and costly when you did it wrong. I made a big mistake there and it really cost the company a lot of time and money.

David: Yet it was awesome.

Wendy: It was awesome.

David: Sounds like you learned a lot there.

I’m curious if you have an example from your career, Wendy, where somebody gave you some advice early in your career that really changed a lot for you?

Wendy: I’ve got one example from early in my career and one from later.

I had an opportunity as a young woman, in my mid-twenties. I got a promotion that required me to move from Jackson, Mississippi to New Orleans. It looked very risky to me. Personally, I’ve gone through a lot of change, so I can deal with personal risk, but I like my professional life to be stable. I was worried about moving and not knowing anyone in New Orleans. My husband couldn’t move with me.

My mentor, who was one of my bosses at the company, said to me, “The risk of saying yes is really very low. The risk of saying no is very high.”

I didn’t get it. My brain was going crazy. He told me, “If you say no, you’re playing small. You have a lot of potential, and you need to go explore that potential. So you don’t know anyone. You’ll meet people.” I’d never thought of that: the risk of yes versus the risk of no.

I told my husband I was moving to New Orleans. Of course he didn’t come. Yes, there was a divorce. Life continues. But that comment about playing small really made me think, and taking his advice changed my life.

The other advice, from later in my life, was from Rob Hayes, who’s a very dear friend at First Round Capital. He was an investor in Get Satisfaction when one of our first term sheets was pulled. The company had no money. We had zero. We were funding it ourselves, we weren’t doing well, and the term sheet got pulled. I didn’t know to be upset about that. I had not had enough experience to freak out when this happened.

Rob understood what it meant, and we met at a coffee shop. He asked me what we were going to do, and I told him that we would keep looking for money and I would invest and we would keep going.

I loved this company, and he was just like, “Wow.” Then he said: “I support you.” For Rob, if I thought there were conditions that we could build around, he was going to support me.

Brad: In 60 seconds or less. What does Give First mean to you?

Wendy: Give without expectation of return.

David: That’s far less than 60 seconds. I’m going to start using that.

The other thing I’d love to hear about is an example in your life where you’ve seen the power of Give First in action.

Wendy: There are lots of those! Here’s one. I was working with some universities in Cincinnati, and we were doing a coaching workshop, teaching people how to do good coaching or good modeling, showing behaviors by doing them. We were working one day in the engineering school, in a coding class. One of my students went over to a young woman and sat down with her. He said to her, “I can tell you’re struggling with this. What can I do to help?”

No one told him to do this, and I didn’t instruct them to run around the room and help each other out. That was good observation and good modeling. I’m really proud of that. It was very natural, so she didn’t feel awkward.

The more we model this behavior—giving without keeping score, and without needing immediate reciprocity—that will change the scope and slope of the work we do. If you model it suddenly and set expectations suddenly, then people lean in. They learn how.

Brad: That’s great. The last section here is something that we lifted from our friend Harry Stebbings, a quickfire round. We’re going to ask you a handful of short questions and we’d love very, very fast answers to each one of them.

David: Let’s do it. Wendy, what’s your favorite book you’ve read in the last year?

Wendy: Small Fry, by Steve Job’s daughter Lisa.

David: Do you have a favorite charity you support?

Wendy: I support the SPCA because I’m a big dog lover.

David: Tell us about a startup you met recently that you think people should check out.

Wendy: I’m very excited about Pipeline Equity, which happens to be a Techstars company, led by Katica Roy.

David: What’s a city that you think people have to visit before they die?

Wendy: I would say Oxford, Mississippi.

David: You did it. You’re through it. Thanks for joining us, Wendy. It’s been a blast having you.